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Indometacin

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Identification
Molecular formula
C19H16ClNO4
CAS number
53-86-1
IUPAC name
2-[3-(4-fluorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid
State
State

Indometacin is in a solid state at room temperature and is usually available as capsules or as a suspension for oral administration.

Melting point (Celsius)
160.00
Melting point (Kelvin)
433.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
357.79g/mol
Molar mass
357.7870g/mol
Density
1.3775g/cm3
Appearence

Indometacin appears as a white to yellow crystalline powder. It is known for its slightly bitter taste.

Comment on solubility

Solubility of 2-[3-(4-fluorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid

The solubility of 2-[3-(4-fluorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid is a topic of interest due to its unique structural characteristics. This compound exhibits:

  • Moderate solubility in organic solvents: It is generally soluble in polar organic solvents such as dimethyl sulfoxide (DMSO) and ethanol, but poorly soluble in water.
  • Effect of pH: The solubility can significantly vary with changes in pH. In acidic environments, the carboxylic acid group can remain protonated, affecting its solubility.
  • Influence of temperature: Increasing the temperature may enhance solubility, making the compound more soluble at higher temperatures.

As a general observation, compounds with complex structures like this one can often lead to varied solubility profiles, influenced by factors such as:

  1. Functional groups present in their structures.
  2. Interactions with solvents, including hydrogen bonding and dipole interactions.
  3. Crystallinity and molecular packing, which can hinder dissolution.

In conclusion, understanding the solubility of 2-[3-(4-fluorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid is crucial for its applications and formulations in pharmaceutical settings. Careful consideration of solvent choice and environmental conditions will lead to optimal performance in various uses.

Interesting facts

Interesting Facts about 2-[3-(4-fluorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid

2-[3-(4-fluorobenzoyl)-6-methoxy-2-methyl-indol-1-yl]acetic acid is a fascinating compound that showcases the complexities of indole derivatives. This compound is particularly noteworthy for several reasons:

  • Pharmaceutical Relevance: Indole derivatives are significant in medicinal chemistry. Compounds like this one have been studied for their potential roles in anti-inflammatory, analgesic, and even anticancer properties.
  • Fluorine Atom Impact: The presence of a fluorine atom (in the 4-position of the benzoyl group) can greatly enhance the metabolic stability and lipophilicity of the compound, making it more bioavailable.
  • Indole Structure: The indole ring structure is pivotal in many biological activities. Its unique configuration allows for π-stacking interactions with biological macromolecules, which is crucial in drug design.
  • Potential Applications: Due to its multifunctional nature, this compound may find applications beyond pharmaceuticals, including in agrochemicals, dyes, and various organic synthesis processes.
  • Structure-Activity Relationship (SAR): Understanding how modifications to its structure affect biological activity offers insights into designing more effective drugs with fewer side effects.

This compound exemplifies how small alterations in a molecular structure can lead to significant changes in properties and applications. As such, it remains an important subject of study in both synthetic and medicinal chemistry.
In the words of a renowned chemist, "The beauty of chemistry lies in the subtlety of molecular transformations."

Synonyms
25803-21-8
INDOLE-1-ACETIC ACID, 3-(p-FLUOROBENZOYL)-6-METHOXY-2-METHYL-
DTXSID50180462
RefChem:1087346
DTXCID60102953
RU 4486
BRN 1552199
Fluoromethacin
3-(p-Fluorobenzoyl)-6-methoxy-2-methyl-1-indoleacetic acid
Carboxymethyl-1 methyl-2 p.fluorobenzoyl-3 indole [French]
2-[3-(4-fluorobenzoyl)-6-methoxy-2-methylindol-1-yl]acetic acid
5-21-12-00657 (Beilstein Handbook Reference)
Carboxymethyl-1 methyl-2 p.fluorobenzoyl-3 indole
SCHEMBL29463840
NS00006821
Q63398123